Jake Wilkinson is an 18-year-old con man attending Palisades Academy in California. For the past few years, he has not been home to New York for Christmas even though he always promised to make it. A few days before Christmas Eve, his father offers to give him his vintage 1957 Porsche if he is home by 6:00 p.m. Christmas Eve for Christmas dinner. Initially, Jake had traded in his plane ticket to New York for two tickets to Cabo San Lucas to take his girlfriend Allie who is also from New York. She considers the act selfish as Jake knows Allie always returns home for Christmas. Jake reconsiders and trades the tickets back in for New York, and she forgives him.
As Jake is leaving, he is taken captive by a group of bullies and abandoned in the desert dressed as Santa Claus. The group did this as punishment for not getting an exam cheat sheet from Jake, unaware that it was their leader Eddie Taffet who withheld the cheat sheet so he might get Jake out of the way and claim Allie for himself. While Jake is stuck in the California desert, Eddie ends up giving Allie a ride to New York after she thinks Jake has bailed on her once again. Jake has only three days to make it to Larchmont, New York if he wants the car and Allie.
He stumbles upon a few obstacles and opportunities, such as a thief, Nolan, who is driving stolen kitchen goods to his dealer near New York. Jake hitches a ride with him, not knowing that he is a thief. A police officer named Max pulls them over for speeding and becomes suspicious of them, so Jake lies and says that Nolan is his elf and they are donating the goods to the children's hospital. The police officer offers for them to join him, as he is heading in the same direction. At the hospital, an Mexican child reminds Jake, Nolan and Max about the importance of family. Nolan decides to return west and win back his girlfriend, therefore abandoning Jake. Max, recently estranged from his wife, asks Jake to accompany him to Nebraska and help him win his wife Marjorie back. Afterwards, Max and Marjorie buy Jake a bus ticket to New York in return for helping them understand their differences.
Meanwhile, Allie and Eddie continue to head for New York. Instead of staying at a cheap roadside motel, Allie convinces Eddie to stay the night at novelty hotel in a Bavarian village. The village is celebrating the holidays, and a television news reporter is reporting live from the village. Allie and Eddie are unknowingly standing beneath a bunch of mistletoe while the news anchor is reporting live. She asks them to kiss for the camera and as they do, Jake happens to be watching the news report and the kiss between Allie and Eddie whilst waiting at the bus station in Nebraska.
The driver on the bus is determined to stick to the schedule as it is a non-stop bus to New York. Jake wants to stop at the Bavarian village and develops a scheme. He obtains a lunch-cooler, a slab of meat from another passenger's sandwich, writes a girl's name and hospital address on the cooler, and then convinces the whole bus that the cooler contains a liver that needs to be delivered to a little girl at the hospital in the Bavarian Village. The bus passengers convince the drive to speed up and detour to the Bavarian village. Jake finds the village, and locates Allie and Eddie's room. After Allie lets Jake in to the room, Eddie walks out of the shower in a towel and Jake assumes he had slept with Allie (he didn't, Allie made him sleep on top of the quilt in several layers of clothes). Jake and Allie eventually make up, until Jake blurts out that Eddie prevented him from getting his dad's car. Upset that Jake had come to get the car and not herself (which he actually did), Allie storms onto the bus and takes Jake's seat. The driver asks is she's the girl who the organ transplant was for to which she agrees. Upset with Jake's tangle of lies, she tells him off and boards the bus.
Jake and Eddie drive off. Jake tells Eddie that he will go home, win back Allie, and get the car. Eddie, unwilling to be a nice guy (it would be bad for his reputation) and jealous that Jake would not only get Allie but also the Porsche, ends up throwing Jake out of his car somewhere in Wisconsin. Jake decides to enter a Santa Claus race for a chance to win a $1,000 prize to buy a plane ticket to New York. Eddie is arrested after being rude to cops dressed as Christmas trees while policing the race. While registering for the race, Jake meets a nice man, Jeff Wilson, who Jake barely beats in the race. Jake wins the prize, but on his way to the airport the taxi driver informs Jake that Jeff Wilson is actually the mayor of the town. Mayor Wilson usually wins the race every year and uses the prize money to buy turkeys for the needy. Jake feels bad, and asks the cab driver to turn back. Jake leaves the money in the Mayor's mailbox, but is caught in the middle of this good deed by the Mayor. The Mayor offers to set an extra place for Jake, but Jake declines, saying he has somewhere to be that evening, and calls home. Jake talks to his sister, who arranges for a plane ticket for Jake from Madison, Wisconsin. The airline refuses to allow Jake to board the place because he had no photograph identification. Jake decides to stow away in a dog kennel on a cargo plane. From the airport, he stows away on a train, tries to hitch a ride in a car (and ends up riding on the roof), then steals a one-horse open sleigh. When he reaches his street, he apologizes to Allie, and they make up. Jake and Allie ride the one-horse open sleigh to Jake's family home, and arrive at 5:59pm. Jake intentionally waits until after 6:00pm to go inside, so that he won't arrive in time to get the Porsche. When Jake's father offers him the Porsche, explaining that he's only a few seconds late, Jake still refuses, insisting that their time spent fixing it up as father and son isn't done yet.
- Jonathan Taylor Thomas as Jake Wilkinson
- Jessica Biel as Allie Henderson
- Adam LaVorgna as Eddie Taffet
- Gary Cole as Jake's dad
- Eve Gordon as Carolyn Wilkinson
- Lauren Maltby as Tracey Wilkinson
- Andrew Lauer as Nolan
- Sean O'Bryan as Officer Max
- Lesley Boone as Marjorie